EP0126792B1 - Procédé de préparation de hexaméthylcyclotrisiloxane et son application - Google Patents

Procédé de préparation de hexaméthylcyclotrisiloxane et son application Download PDF

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Publication number
EP0126792B1
EP0126792B1 EP83105271A EP83105271A EP0126792B1 EP 0126792 B1 EP0126792 B1 EP 0126792B1 EP 83105271 A EP83105271 A EP 83105271A EP 83105271 A EP83105271 A EP 83105271A EP 0126792 B1 EP0126792 B1 EP 0126792B1
Authority
EP
European Patent Office
Prior art keywords
organopolysiloxane
cyclotrisiloxane
prepared
substances
hexamethylcyclotrisiloxane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP83105271A
Other languages
German (de)
English (en)
Other versions
EP0126792A1 (fr
Inventor
Franz-Heinrich Dr. Dipl.-Chem. Kreuzer
Helmut Dr. Dipl.-Chem. Gebauer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Consortium fuer Elektrochemische Industrie GmbH
Original Assignee
Consortium fuer Elektrochemische Industrie GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Consortium fuer Elektrochemische Industrie GmbH filed Critical Consortium fuer Elektrochemische Industrie GmbH
Priority to AT83105271T priority Critical patent/ATE22896T1/de
Priority to DE8383105271T priority patent/DE3366928D1/de
Priority to EP83105271A priority patent/EP0126792B1/fr
Priority to JP58112981A priority patent/JPS59222495A/ja
Priority to US06/524,009 priority patent/US4620023A/en
Priority to US06/614,391 priority patent/US4863723A/en
Publication of EP0126792A1 publication Critical patent/EP0126792A1/fr
Application granted granted Critical
Publication of EP0126792B1 publication Critical patent/EP0126792B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A61L9/044—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating with the help of an organic compound other than a macromolecular compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring

Definitions

  • the invention relates to a process for the preparation of hexamethylcyclotrisiloxane by depolymerizing linear, branched or crosslinked organopolysiloxane, which consists of at least 50 mole percent of dimethylsiloxane units, while heating to at least 350 ° C. and at the same time distilling off the cyclic dimethylpolysiloxanes formed, characterized in that this Depolymerization takes place in the absence of substances attacking a siloxane grouping.
  • linear, branched or crosslinked organopolysiloxanes which consist of at least 50 mole percent of dimethylsiloxane units
  • all linear, branched or crosslinked organopolysiloxanes which consist of at least 50 mole percent of dimethylsiloxane units can also be used in the context of the invention and from which they have thus far been obtained by rearrangement of Siloxane groups cyclic dimethylpolysiloxanes could be prepared.
  • Linear or practically linear or cross-linked organopolysiloxanes consisting of at least 95 mole percent of diorganosiloxane units, the organic groups of which are at least 95 mole percent methyl groups, are preferred.
  • the other organic groups optionally present in addition to methyl groups in the organopolysiloxanes used in the invention are preferably ethyl, vinyl or phenyl groups or mixtures of at least two such other groups.
  • the particular triorganosiloxane) monoorganosiloxane or Si04n units or mixtures of at least two are optionally in addition to other siloxane Diorganosiloxaneinhe i th present of such other units.
  • Organopolysiloxane used in the process according to the invention can be present in more or less pure form, but at least essentially free of substances attacking a siloxane group at 350 ° C.
  • Organopolysiloxane used in the method according to the invention can also, e.g. in the form of crosslinkable, partially or completely crosslinked elastomers, which usually contain, in addition to crosslinkable or crosslinked organopolysiloxane, customary auxiliaries for elastomer production, such as fillers, pigments, crosslinking catalysts, such as organic tin compounds or crosslinking catalyst cleavage products, as long as they are at least essentially free of substances attacking a siloxane group at 350 ° C.
  • organopolysiloxane can be used in the process according to the invention, but also mixtures of different types of organopolysiloxanes can be used.
  • the heating in the process according to the invention is preferably carried out at at most 800 ° C.
  • a siloxane grouping i.e. a grouping of the formula
  • organopolysiloxane are not e.g. at temperatures of at least 350 ° C from e.g. tin oxides formed from organic tin compounds, but probably e.g. at 500 ° C, for example, the alkali content of standard device glass.
  • the presence of substances attacking a siloxane grouping can now be avoided according to the invention.
  • the organopolysiloxanes used in the process according to the invention but also the devices used in the process according to the invention, insofar as their surface has a temperature of at least 350 ° C., in the technically feasible extent of substances which attack a siloxane grouping at 350 ° C. , be free.
  • linear, branched or crosslinked organopolysiloxane which consists of at least 50 mole percent of dimethylsiloxane units, is preferably heated to at least 350 ° C. in containers made of iron or steel, copper, nickel or chromium or of alkali-free alloys of these metals.
  • a gas which is inert to this organopolysiloxane such as nitrogen, can be passed through this organopolysiloxane.
  • the process according to the invention is preferably carried out at the pressure of the surrounding atmosphere, that is to say at 1 bar or approximately 1 bar. However, higher or lower pressures can be used if desired.
  • the heating of linear, branched or crosslinked organopolysiloxane which consists of at least 50 mole percent of dimethylsiloxam units, can be carried out to at least 350 ° C. with stirring or circulation.
  • the process according to the invention can be carried out batchwise, semi-continuously or fully continuously.
  • the hexamethylcyclotrisiloxane produced according to the invention is excellently suitable as a carrier for fragrances, it being possible for this carrier to be in a mixture with other carriers such as tetramethylcyclobutanedione.
  • the V4A steel mentioned in the examples consists of 18 weight percent chromium, 11 weight percent nickel, 2 weight percent molybdenum, 0.07 weight percent carbon and iron as the balance.
  • a vessel made of V4A steel with an inner diameter of 90 mm and a tube of 180 mm, which is electrically heated to 600 ° C 160 ml (measured or normal conditions) of nitrogen are continuously added from above at the same time, but through two different lines Minute and 510 ml per hour in the terminal units each have a Si-bonded hydroxyl group containing dimethylpolysiloxane with a viscosity of 100 mPa.s at 25 ° C.
  • the cyclic diorganopolysiloxanes formed and distilled off during the heating are condensed in a descending cooler attached to the vessel.
  • the vessel in which organopolysiloxane is heated contains, in addition to these organopolysiloxane and nitrogen, 0.5 g in each case of an alkali compound which attacks a siloxane group, as indicated in Table 1.
  • a crosslinked organopolysiloxane 100 parts of a dimethylpolysiloxane each having a sigebonded hydroxyl group in the terminal units and having a viscosity of 500 mPa.s with 3 parts of ethyl polysilicate with an SiO 2 content of 40% and 1 part of dibutyltin diacylate, the acylate groups each derived from a mixture of 9 to 11 carbon atoms per molecule having carboxylic acids, in which the carboxyl group is bound to a tertiary carbon atom in at least 90% of the acids (so-called "dibutyltin diversat").
  • the mass is poured into a mold and left to crosslink at room temperature.
  • the organopolysiloxane elastomer prepared in this way is heated to 500 ° C. in the device described in Example 1 without the addition of another substance. The following result is obtained:
  • the weight ratio of trisiloxane to tetrasiloxane is 4.54.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Silicon Polymers (AREA)
  • Fats And Perfumes (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

Claims (2)

1. Procédé de préparation de l'hexaméthylcyclotrisiloxane par dépolymérisation en chauffant à des température d'au moins 350°C d'un poly-organosiloxane linéaire ramifie ou réticulé, constilué, pour au moins 50 4b en moles, de motifs diméthylsiloxanes, et séparation simultanée par distillation, des poly- diméthylsiloxanes cycliques qui se sont alors formés, procédé caractérisé en ce qu'on effectue cette dépolymérisation par voie thermique en l'absence de corps attaquant un groupement siloxanique.
2. Procédé selon la revendication 1, caractérisé en ce que la dépolymérisation du poly-organosiloxane
est effectuée dans un récipient en fer ou en acier, en cuivre, en nickel ou en chrome, ou en alliages de ces métaux dépourvus de composés alcalins.
EP83105271A 1983-05-27 1983-05-27 Procédé de préparation de hexaméthylcyclotrisiloxane et son application Expired EP0126792B1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AT83105271T ATE22896T1 (de) 1983-05-27 1983-05-27 Verfahren zur herstellung von hexamethylcyclotrisiloxan und eine verwendung des so hergestellten cyclotrisiloxans.
DE8383105271T DE3366928D1 (en) 1983-05-27 1983-05-27 Process for the preparation of hexamethyl cyclotrisiloxane and an application of the cyclotrisiloxane so prepared
EP83105271A EP0126792B1 (fr) 1983-05-27 1983-05-27 Procédé de préparation de hexaméthylcyclotrisiloxane et son application
JP58112981A JPS59222495A (ja) 1983-05-27 1983-06-24 ヘキサメチルシクロトリシロキサンの製造方法
US06/524,009 US4620023A (en) 1983-05-27 1983-08-17 Method for preparing hexamethylcyclotrisiloxane and uses for the same
US06/614,391 US4863723A (en) 1983-05-27 1984-05-25 Method for preparing hexamethylcyclotrisiloxane and uses for the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP83105271A EP0126792B1 (fr) 1983-05-27 1983-05-27 Procédé de préparation de hexaméthylcyclotrisiloxane et son application

Publications (2)

Publication Number Publication Date
EP0126792A1 EP0126792A1 (fr) 1984-12-05
EP0126792B1 true EP0126792B1 (fr) 1986-10-15

Family

ID=8190495

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83105271A Expired EP0126792B1 (fr) 1983-05-27 1983-05-27 Procédé de préparation de hexaméthylcyclotrisiloxane et son application

Country Status (5)

Country Link
US (1) US4620023A (fr)
EP (1) EP0126792B1 (fr)
JP (1) JPS59222495A (fr)
AT (1) ATE22896T1 (fr)
DE (1) DE3366928D1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4863723A (en) * 1983-05-27 1989-09-05 Consortium Fur Elektrochemische Method for preparing hexamethylcyclotrisiloxane and uses for the same
US4764631A (en) * 1988-01-15 1988-08-16 Dow Corning Corporation Preparation of cyclopolydiorganosiloxanes via vapor phase rearrangement
US4895967A (en) * 1988-09-26 1990-01-23 General Electric Company Method for making cyclic poly(siloxane)s
DE4126319A1 (de) * 1991-08-08 1993-02-11 Wacker Chemie Gmbh Verfahren zur pyrolyse von silikonkautschukvulkanisaten
EP0546747A1 (fr) * 1991-12-05 1993-06-16 General Electric Company Procédé de polymérisation
US6262289B1 (en) 1997-06-11 2001-07-17 Kaneka Corporation Process for preparing cyclic oligosiloxanes
GB2331992A (en) * 1997-12-02 1999-06-09 Dow Corning Process for making cyclic organotrisiloxanes
JP4663838B2 (ja) 2000-01-28 2011-04-06 東レ・ダウコーニング株式会社 環状シロキサンの製造方法
EP2077123A1 (fr) * 2008-01-04 2009-07-08 V. Mane Fils Gel anhydre transparent comportant du parfum

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2438478A (en) * 1942-02-26 1948-03-23 Corning Glass Works Method of preparing silicones and product thereof
US2618648A (en) * 1951-08-28 1952-11-18 Gen Electric Preparation of hexamethylcyclotrisiloxane
BE537467A (fr) * 1954-04-21
US2860152A (en) * 1956-04-26 1958-11-11 Dow Corning Method of producing cyclic diorganosiloxanes
JPS5250791B2 (fr) * 1972-12-30 1977-12-27
US3846464A (en) * 1973-11-27 1974-11-05 Gen Electric Process for preparing cyclic methylvinylsiloxanes
US4111973A (en) * 1977-12-01 1978-09-05 General Electric Company Process for producing a cyclotrisiloxane in a cracking reaction

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Noll, Chemie u. Technologie der Silikone, Weinheim1968, S. 201, 195 *

Also Published As

Publication number Publication date
US4620023A (en) 1986-10-28
DE3366928D1 (en) 1986-11-20
ATE22896T1 (de) 1986-11-15
JPS6213357B2 (fr) 1987-03-25
EP0126792A1 (fr) 1984-12-05
JPS59222495A (ja) 1984-12-14

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